Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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Guest favourite

Cottage in Ashland

4.96 out of 5 average rating, 364 reviews

Charming very well appointed cottage !

The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 2 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If quiet is what you are looking for, the cottage will meet all your needs.

Nov. 2 – 9

$198 CAD per night

Guest favourite

Apartment in Ashland

4.94 out of 5 average rating, 255 reviews

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (low ceiling) Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Private parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Aug. 22 – 29

$201 CAD per night

Guest favourite

Guesthouse in Ashland

4.97 out of 5 average rating, 431 reviews

Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

Dec. 14 – 21

$270 CAD per night

Guest favourite

Guesthouse in Ashland

4.94 out of 5 average rating, 106 reviews

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

Feb. 22 – Mar. 1

$169 CAD per night

Guest favourite

Guesthouse in Ashland

4.98 out of 5 average rating, 507 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Dec. 10 – 17

$221 CAD per night

Guest favourite

Farm stay in Ashland

5.0 out of 5 average rating, 117 reviews

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

Sep. 6 – 13

$176 CAD per night

Guest favourite

Cabin in Ashland

4.94 out of 5 average rating, 224 reviews

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin has remodeled upgrades and is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakepeare Fetival, Plaza shops, beautiful Lithia Park and Resturants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the pituresque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings!

Jan. 5 – 12

$158 CAD per night

Guest favourite

Apartment in Ashland

4.95 out of 5 average rating, 640 reviews

Modern Crash Pad | Pet Friendly | West Wing

NEW! Upgraded to KING bed!! A modern suite located steps away from the Ashland conference center and just minutes to downtown. Step into this light filled space which boasts stunning walk in shower, antique brass fixtures, and convenience kitchenette. Thoughtfully designed including heated bathroom tiles. Enjoy the breathtaking views of Grizzly Peak, and the local non-commercial airport. 1 pet welcome with fee. Note that we do not have a fenced yard. (#18-243).

Dec. 9 – 16

$187 CAD per night

Guest favourite

Camper/RV in Ashland

4.88 out of 5 average rating, 917 reviews

Cozy camping close to town

The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, French press, hot water kettle, lending library, and games; this adorable camper is both functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

Apr. 18 – 25

$73 CAD per night

Guest favourite

Guesthouse in Central Point

4.94 out of 5 average rating, 703 reviews

BEE WELL Organic Spa Garden Studio

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

Aug. 13 – 20

$126 CAD per night

Guest favourite

Guesthouse in Ashland

4.9 out of 5 average rating, 337 reviews

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

Oct. 16 – 23

$228 CAD per night

Guest favourite

Home in Ashland

4.95 out of 5 average rating, 180 reviews

Coyote Moon

Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.8 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island. Perfect for a romantic couples getaway and also great for those visiting Ashland for the Oregon Shakespeare Festival. Wireless internet and Netflix and internet TV.

Jan. 11 – 18

$344 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Ashland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Ashland's top sights

Lithia Park198 locals recommend

Oregon Shakespeare Festival267 locals recommend

Ashland Springs Hotel3 locals recommend

Ashland's Own Shop'n Kart38 locals recommend

Brickroom76 locals recommend

Oregon Cabaret Theatre50 locals recommend

Other great vacation rentals in Ashland

Guest favourite

Tiny homes in Shady Cove

4.95 out of 5 average rating, 198 reviews

Modern Tiny House w/ Hot Tub

Sep. 27 – Oct. 4

$220 CAD per night

Guest favourite

Yurt in Grants Pass

4.97 out of 5 average rating, 652 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

Feb. 14 – 21

$141 CAD per night

Guest favourite

Cottage in Ashland

4.97 out of 5 average rating, 424 reviews

Victorian Garden Carriage House

Jan. 5 – 12

$334 CAD per night

Guest favourite

Home in Ashland

4.82 out of 5 average rating, 17 reviews

Cowslip's quiet, central, Cuckoo-Bud Suite

Feb. 2 – 9

$102 CAD per night

Guest favourite

Guest suite in Ashland

4.93 out of 5 average rating, 74 reviews

Summer’s Night Cottage 8 minute walk to Downtown

Dec. 9 – 16

$167 CAD per night

Guest favourite

Guesthouse in Ashland

5.0 out of 5 average rating, 54 reviews

Countryman-Fox Carriage House

Nov. 29 – Dec. 6

$220 CAD per night

Guest favourite

Guesthouse in Ashland

4.91 out of 5 average rating, 44 reviews

Neil Creek Cottage

Feb. 25 – Mar. 4

$148 CAD per night

Guest favourite

Guesthouse in Ashland

4.92 out of 5 average rating, 61 reviews

Ashland country guest house

Mar. 3 – 10

$216 CAD per night

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Quick stats about vacation rentals in Ashland

Total rentals	280 properties
Rentals with dedicated workspaces	140 properties have a dedicated workspace
Rentals with a pool	20 properties have a pool
Pet-friendly rentals	100 properties allow pets
Family-friendly rentals	100 properties are a good fit for families
Total number of reviews	19K reviews

Vacation rentals in Ashland

Top-rated vacation rentals in Ashland

Cottage in Ashland

Apartment in Ashland

Guesthouse in Ashland

Guesthouse in Ashland

Guesthouse in Ashland

Farm stay in Ashland

Cabin in Ashland

Apartment in Ashland

Camper/RV in Ashland

Guesthouse in Central Point

Guesthouse in Ashland

Home in Ashland

Vacation rentals for every style

Cottages

Houses

Cabins

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Other great vacation rentals in Ashland

Tiny homes in Shady Cove

Yurt in Grants Pass

Cottage in Ashland

Home in Ashland

Guest suite in Ashland

Guesthouse in Ashland

Guesthouse in Ashland

Guesthouse in Ashland

Quick stats about vacation rentals in Ashland

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore